Supramolecular Control of Oligothienylenevinylene−Fullerene Interactions:  Evidence for a Ground-State EDA Complex

McClenaghan, Nathan D.; Grote, Zacharias; Darriet, K.; Zimine, Mikhail; Williams, René M.; Cola, Luisa De; Bassani, Dario M.

doi:10.1021/ol047527r

Cited by 50 publications

(27 citation statements)

References 26 publications

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“…The fullerene unit was reorganized and placed between two TV side arms of the receptor unit (2.214, Chart 2.35). 313 Due to the close proximity of the redox-active fullerene and TV moieties within the assembly, strong ground-state D-A interactions were observed. Ultrafast time-resolved transient absorption measurements revealed a fast photoinduced electron transfer from the TV donor to the fullerene acceptor unit, suggesting a strong binding between the redox centers.…”

Section: Scheme 239mentioning

confidence: 99%

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

2009

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Amaresh Mishra (right) received his Ph.D. degree in 2000 from the Sambalpur University, India, under the coguidance of Prof. G. B. Behera and Prof. R. K. Behera, working on dye-surfactant interactions in microheterogeneous media. He started his postdoctoral research career in 1999 at the University of South Florida, Tampa, and subsequently at the University of Akron, Ohio, working with Prof. G. R. Newkome, where he gained knowledge in the area of supramolecular and dendrimer chemistry. Later, he joined the Tata Institute of Fundamental Research, Mumbai, in 2002 as a Visiting Fellow working with Prof. N. Periasamy, where he was involved in the synthesis and photophysical studies of organic light emitting materials. In 2005, he joined in the group of Prof. Peter Ba ¨uerle, University of Ulm, Germany, as an Alexander von Humboldt Fellow. His present research interests are centered on chemistry of functional oligothiophenes, donor-acceptor-based conjugated dyes, and metal complexes toward applications in solar energy conversion and molecular electronic and photonic devices. Chang-Qi Ma (left) received his bachelor's degree in chemistry from Beijing Normal University in 1998. In 2003 he obtained his Ph.D. degree at the Technical Institute of Physics and Chemistry, Chinese Academy of Sciences in Beijing with Professor B.-W. Zhang. After that he was a postdoctoral research assistant at Heriot-Watt University in Edinburgh, U.K., with Dr. G. Cooke, until he joined the research group of Prof. P. Ba ¨uerle at the University of Ulm in 2004 as an Alexander von Humboldt fellow, where he is currently a research associate. His main research interests focus on the design and synthesis of novel π-conjugated organic materials for the application in organic electronics, e.g. organic solar cells.Peter Ba ¨uerle (center) received his Ph.D. in organic chemistry from University of Stuttgart (Germany, 1985) working with Prof. F. Effenberger. After a postdoctoral year at MIT, Boston, Massachusetts, in the group of Prof. M. S. Wrighton, he carried out independent research at the University of Stuttgart and received his habilitation (1994). After being Professor of Organic Chemistry at the University of Wu ¨rzburg (Germany, 1994-95), he became Director of the Institute for Organic Chemistry II and Advanced Materials at the University of Ulm (Germany, since 1996). Current research interests of the group include development of novel organic semiconducting and conducting materials, in particular, conjugated poly-and oligothiophenes. Synthetic strategies and new reactions for their functionalization, structure-property relationships, self-assembling properties, and applications in electronic devices, in particular organic solar cells, are investigated. Results have been published in about 200 peer-reviewed scientific papers, 3 book chapters, and 7 patents. For his work in the field of plastic electronics he was awarded with the Rene ´Descartes Prize of the European Union (2000). Guest Professorships at the University of Osaka (Japan, 2002), U...

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Section: Scheme 239mentioning

confidence: 99%

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

2009

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“…Photoexcitation of the fullerene chromophores to their 1.76-eV excited state is followed, in one of the three forms of 11, by a charge separation process generating a 1.15-eV radical ion pair state. On average, this state perdures for at least 1.5 s, which is comparable to the performance of other noncovalent C 60 -based hybrids (in which electron transfer occurs basically via through-space interactions) (14,15,(31)(32)(33) and is superior to that of typical covalent C 60 -exTTF conjugates (25)(26)(27)(28). The structure of 11 in principle allows its extension to form a nanotubular battery along which electron donors and electron acceptors alternate and also suggests the possibility of designing molecular switches based on dynamic control of interconversion between the electroactive isomer 11-Z and the inactive isomers 11-X and 11-Y.…”

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confidence: 52%

Electron transfer in Me-blocked heterodimeric α,γ-peptide nanotubular donor–acceptor hybrids

Brea

Castedo

Granja

et al. 2007

Proc. Natl. Acad. Sci. U.S.A.

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Bio-inspired cyclopeptidic heterodimers built on ␤-sheet-like hydrogen-bonding networks and bearing photoactive and electroactive chromophores on the outer surface have been prepared. Different cross-strand pairwise relationships between the side chains of the cyclic ␣,␥-peptides afford the heterodimers as three nonequivalent dimeric species. Steady-state and time-resolved spectroscopies clearly show an electron transfer process from -extended tetrathiafulvalene, covalently attached to one of the cyclopeptides, to photoexcited [60]fullerene, located on the complementary cyclopeptide. The charge-separated state was stabilized for up to 1 s before recombining and repopulating the ground state. Our current example shows that cyclopeptidic templates can be successfully used to form light-harvesting/lightconverting hybrid ensembles with a distinctive organization of donor and acceptor units able to act as efficient artificial photosystems.cyclic peptide nanotubes ͉ fullerenes ͉ self-assembly P eptide-based tubular systems are being widely used to mimic Nature's channel-forming structures (1). Stable architectures ranging from ␤-helices to stacked macrocycles can self-assemble through multiple hydrogen-bonding interactions between and/or within peptide units with backbones capable of adopting an appropriate curvature. However, although a variety of versatile strategies have been developed to produce peptide tubes (2, 3), comparatively little has been done in the way of controlled functionalization of their inner and/or outer surfaces so as to fit them for specific tasks (4).Peptide nanotubes (PNs) or nanotube segments formed by the self-stacking of two or more cyclic peptides (2, 3, 5) are notable examples of the ''bottom-up'' approach to functional nanostructures. These self-assembled PNs have found application in biological and medical research and materials science (6-10). Their self-assembly is brought about by hydrogen bonding between their constituent cyclic peptides (CPs). The chirality of the amino acid residues of the CPs is such that the CP backbone forms an essentially flat ring with its CAO and NOH groups oriented nearly perpendicular to the ring plane and its side chains radiating outward. This conformation allows each face of the CP to take part in a ␤-sheet-like hydrogen-bond array with another CP that, depending on the sequence of amino acid residues in the CPs, must be oriented either parallel or antiparallel to the first (11-13). Scheme 1 shows an example of the antiparallel stacking of CPs formed of alternating ␣-and ␥-amino acid residues (␣,␥-CPs). Note that the precise orientation of side chains in planes perpendicular to the CP rings depends on backbone interactions within each ring.Within the nanobiomaterials field, one of the most actively pursued goals is the design of highly efficient and highly directional electron transfer mimics of the photosynthetic systems of plants and bacteria. In principle, self-assembled PNs bearing an appropriate array of photoactive and electroactive units might ac...

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“…The same group has reported another study on decay of EDA complexes of aniline and 2,4-dimethylaniline with naphthalene-1,4,5,8-tetracarboxylic dianhydride [31]. In addition, several such kind of reactions are reported in recent years [9,10,[32][33][34][35][36][37][38].…”

Section: Introductionmentioning

confidence: 90%

Electron donor–acceptor interaction of 3,4-dimethylaniline with 2,3-dicyano-1,4-naphthoquinone

Neelgund

Magadum

Budni

2011

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Supramolecular Control of Oligothienylenevinylene−Fullerene Interactions: Evidence for a Ground-State EDA Complex

Cited by 50 publications

References 26 publications

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

Electron transfer in Me-blocked heterodimeric α,γ-peptide nanotubular donor–acceptor hybrids

Electron donor–acceptor interaction of 3,4-dimethylaniline with 2,3-dicyano-1,4-naphthoquinone

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